


Pretty Pirates and Pink Dresses

by HornyHistories (sherlocked221)



Series: Horny Histories [5]
Category: Horrible Histories
Genre: Crossdressing, M/M
Language: English
Status: Completed
Published: 2018-10-05
Updated: 2018-10-05
Packaged: 2019-07-25 15:32:49
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings, No Archive Warnings Apply
Chapters: 1
Words: 2,574
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16200428
Author URL: https://archiveofourown.org/users/sherlocked221/pseuds/HornyHistories
Summary: These actors on Horrible Histories are all men, not boys. Highly immature, childish and horny men, but at least by their ages are technically men.Mat has to dress up for a Putrid Pirate sketch, and Ben quite likes what he ends up wearing.He likes it quite a lot.





	Pretty Pirates and Pink Dresses

**Author's Note:**

> I haven't checked over this one, so... forgive me.

Dressing in drag. It seemed to be written into every comedian’s contract, especially those on a kid’s TV show. Horrible Histories wasn’t that much like a pantomime, but it was starting to feel like one when Mat squeezed into a golden, Georgian era dress and pulled on a matted, brunette wig. The latter was no novelty. He’d worn stranger wigs dressed as a man. And, as in the sketch he would play with the strands, he found it strangely comforting to do so when they weren’t filming. But the dress? To be honesty, he was quite used to it. He wore togas and roman amour and kilts and scraps of fabric mimicking mammoth fur that cavemen might’ve worn. He’d been in stranger outfits, and probably in dresses too, so why he bothered to look in his dressing room mirror and feel just a little self-conscious, he had no idea.

He actually liked dressing up. Most of the guys on Horrible Histories did. Jim particularly seemed to take much joy in his characters, wandering out of his dressing room, padded out in fat suits, or playing with his long, Viking beard, and would ask who agreed he suited that look. And he always seemed to. Simon seemed happiest to be undressed entirely, and Martha had really grown accustomed to wandering around, going about her daily business, in the most uncomfortable looking dresses you could imagine. Mat hadn’t been clad in a corset and huge skirt very often, but he really thought this sensation wasn’t something anyone could really get used to. Or at least, he couldn’t. There was actual boning in the bodice of the dress, which jabbed into his dress, and as he wandered about from wardrobe to his dressing room to make-up, he kept tripping up on his own petticoat.

Thankfully, the sketch wasn’t too demanding. All he needed to do was stand on a set, deliver a few lines drenched in pirate slang and give a frustrated look towards the camera as his colleagues fought over the ‘pink dress.’

What made Mat laugh, as he checked his phone for the last time before he had to be on set, was that he could see this sketch happening in real life, in the wardrobe. If you got the crew together and gave them an option of what dress they could clad themselves in, you bet there would be one colour everyone would want. Jim, Larry and Simon would certainly want pink, with a bright pink lipstick to match. Martha and Ben would probably be the only two sensible enough to take whatever was left and Mat? Well, he would probably snatch the dress the other three were fighting about, and flaunt his victory in front of them for the rest of the day. The producers would certainly be throwing their heads into their hands, wishing they hadn’t given them a choice at all.

Laughing at the image- and wishing he was wearing the dress he’d imagined, for some reason- Mat tossed his phone onto the table in his dressing room and stumbled towards the door. He felt heavy and clumsy, not even from the weight of the fabric swishing around him. It was instead the feeling of his trainers and socks, and the vest he had tucked beneath the corset. Strange how that had begun to feel more alien to him than the dress itself.

“Mat?”

The studio was always bustling full of people, people going about their business and paying little attention to the actors wandering around in strange outfits. Mat hardly ever took much notice of others when he made his way to the set just as others paid no attention to him. Only, he wished he had this time. As his eyes darted towards the voice calling his name, pink coloured his cheeks.

“Oh, hey…”

Ben was dressed up too, though not in a huge frock, not even in something ridiculous enough for Mat to feel a little more on the same page as him. Ok, so in one hand, the older man clutched a plastic hook, making it look as though he’d lost the limb, but that was cool really. If nothing else, it fit the whole pirate look they were going for.

As for Mat, he just felt like a skinny guy clad in a gown, make-up smeared on his face and strands of his wig getting caught in his eyelashes as he blinked.

He felt just a little stupid.

Especially when Ben was smirking, the cheeky grin brightening up his usually moodily handsome face. He leant cheerily against the wall with one arm resting up by his head, looking less like a pirate and more himself, behind a thick mask of faux dirt applied as heavily as Mat’s make-up.

“Looking good.” He teased.

“Oh yeah, yeah, laugh it up, I bet I’m the funniest thing you’ve ever seen.” Mat chuckled back. Shyly, he pushed a few strands of hair out of his face and fixed that one line of boning jutting into his stomach as he sighed. Perhaps filming was going to be more tedious than he expected if he was going to be the butt of the jokes today.

However, neither he nor Ben moved towards the set to get the filming underway. As though they had the same thought, they both stood there, glancing at one another, until finally, Ben replied to what Mat had said, seemingly ages ago, before their conversation had died into silence.

“No, actually.”  

It took a moment for Mat to remember what he had said.

Oh yeah, they were teasing him.

“No?” He laughed back, unconvinced. But Ben’s expression was quite a lot softer than if he had been taunting. He had a dark streak to him, a sharp cheekiness that made you wonder whether he was being genuine or not. This expression, however, as his eyes fell down Mat’s body and back up again, left little doubt that he meant what he had said. Mat wasn’t the funniest thing Ben had seen. Ben wasn’t finding this funny in the way his mate expected.

“Then what?”

“Then what what?” Ben laughed back. He wasn’t all that good at flirting. This was about all he could manage, unless he was to break out the really cheesy lines, those which had almost a 100% chance of falling flat. He had hoped an amused gaze and cryptic comments would serve him well enough.

It had before, with the very man who stood before him, narrowing his pretty eyes.

“Well if I’m not the most ridiculous thing you’ve ever seen, what’s making you smile?”

Ben’s smirk only widened. What was making him smile? Well, he wasn’t sure he could exactly say it out loud, at least not in what could be a busy corridor. He couldn’t announce it to the whole crew (even if the corridor remained pretty silent at that moment.)

He thought it best, instead, to kick off the wall and stride up to Mat, crowding him against his dressing room door. The smaller man made wider by the thick dress, pressed himself against the support behind him, watching as Ben leant down and hovered his lips over Mat’s attending ear. He watched until Ben’s face was hidden beside his cheek, at which time he closed his eyes, as though to hear him better.

“I was smiling, because I had an awful thought.”

“What thought?” Mat whispered, eyes still shut, heart beginning to react to the feeling of Ben so close in such a public place, possibly full of their friends who had no idea about… _them two_.

It was even worse when Ben chuckled breathily, and Mat could feel it against his jawline. That time, it wasn’t his heart just his heart that reacted.

“I was just thinking…” The taller man continued, “…how very naughty it would be if I hiked up your skirt and had you before we started filming.”

At that moment, Ben’s hand’s wandered. They fell to Mat’s waist and began gathering the fabric of his skirt between his fingers. Mat felt a breeze on his shins as the skirt drew up higher.

“We don’t have time…” He breathed, half-heartedly. Though he knew he was probably due on set around about now, there was no way he was going to stop Ben. “…do we?”

It was by total accident, of course, that upon deciding the studio could wait for them, Mat suddenly caught the handle of the door with his elbow and the door swung open, though it may not have looked so much like that, since neither he nor Ben lost their footing at all. It was almost as though they had meant to open the door and pile into the small room, firmly shutting the door behind them using Mat’s back quite conveniently pressed against it. But, later, Mat would swear that he hadn’t meant to at all: it was a happy accident.

A very happy accident.

Of course, at the time, Ben didn’t question it. He wasn’t exactly thinking straight long enough to tease Mat about his willingness and eagerness. He himself was displaying far too many traits of those too to be chiding anyone else for it, especially when he dropped the fake hook in his hand and reached for Mat’s backpack, knowing that there was a tube of something slippery they could use in that moment.

Upon finding lube, he set about coating a finger in it, while Mat ground his butt into Ben’s growing erection. He even had to stop for a moment, grasp Mat’s hips and jerk himself off against the layer of fabric covering the boy’s behind. It was too much, too intoxicating. Easily, he could’ve come like that, but where was the fun? They didn’t have much time as it was, but that didn’t mean they were going to half-arse it. At least, Ben had no intentions of such a thing. Even if it meant risking getting caught when one of their mates or fellow crew members came knocking to see what was keeping them, Ben was determined to get off properly.

Just as he had fantasied in that brief moment upon seeing Mat all dressed up, Ben took a handful of skirt and drew it up to the hip. He hooked it over Mat’s back, exposing one of Mat’s boxer-clothed butt cheeks. Since he was one hand short, one slicked up already, it took a moment for him to move enough of the dress out the way and pull down Mat’s boxers. Once he had, though, he wasted no time. He gently pushed his slicked finger inside his friend, and leant over Mat’s whimpering stature to kiss him tenderly on the back of the ear.

“Feel alright?” He breathed. Mat could hardly reply, save for nodding enthusiastically. Ben noticed a sheen of sweat beading at Mat’s temples. That dress must’ve been pretty hot. As hot as it looked.

Like that, bent over his mate so that he could pepper kisses down his neck, Ben thrust his finger in and out of Mat, then added another. Mat sucked in a gasp through gritted teeth, and stifled his moans from that moment on into his own hand. Ben could’ve sworn he heard the boy cry out his name. That made him strain in his trousers.

Three fingers Ben fucked Mat with until he was adequately stretched, then, with his free hand that had been firmly gripping Mat’s hip, he unzipped his trousers, pulled himself out of them and palmed himself with a large dose of lube. That didn’t feel half as good as when he had been rutting against Mat, or when, in the next moment, he pushed the tip of his erection to meet with Mat’s hole. Oh, nothing he knew of felt half as good as that. He had to muffle his own groans with the back of his wrist.

Only problem now was that both his hands were covered in lube and he feared getting any on the costume Mat wore, or even on his own. Before he lost all control and started fucking the boy bent in front of him, he cast a gaze towards the table behind him. Tissues. He needed tissues.

“In… my… bag…” He heard Mat pant.

“What?”

“Tissues. I’ve got a packet in my bag. F- hurry up will you.”

Ben chuckled to himself, both at the fact Mat knew what he needed, and also at his desperation. Following his instruction, he sought out the packet of tissues and hurried back, hands now free to grasp wherever he pleased.

And with nothing else holding them back, and time rapidly running out, he pushed inside Mat, bending over him to swallow each cry the younger man threatened to make as he adjusted to being stretched. They then whimpered and groaned together, drawing nearer and nearer climax with every thrust.

Ben finished first, losing all control as he slammed into Mat, and Mat into the door. Beneath the deafening pleasure he felt, he was sure he was probably making too much noise, not from his mouth, but by pushing into Mat roughly enough to shake the hinges off the door, if he wasn’t careful, not to mention the sound of skin slapping against skin accompanied by the rustling of heavy fabric.

Then, once he’d come and pulled himself out of Mat, shaking and quivering still with pleasure, he turned the boy around, fell to his knees and swallowed Mat’s own leaking erection, bringing him to a swift, and slightly less messy, climax.

Soon, they both were weak and tired, sweating and panting and laughing as they met one another’s gaze. Mat was holding up the back of his skirt, Ben held up the front. Mat’s chest heaved inside his corset while Ben searched both for the tissues he’d dropped, and the hook he needed for the sketch. Because it dawned on them both, as they came down from their high, that they were going to have to film after this. Right after it. Like, one of their producers could be looking from them right that minute. And instead of being all that panicked, they found it quite funny.

“Fucking hell, what have we just done?” Mat laughed, tossing his head back against the door and sighing loudly. Ben, tenderly, began cleaning his friend up as best he could.

“I don’t know,” He replied, “But I think we need a quick trip to the loos.”

“I do too.” Mat agreed.

Sufficiently dressed and, seeing as they hadn’t been called as of yet, after having make out a little post-fucking, they shuffled out into the studio, and headed as inconspicuously towards the toilets as they could, when Mat was still a little unstable on shaking legs, and Ben held his hands out in need of washing them. When they got to the loos, there stood one of their mates, washing his hands, thankfully unaware of what had just gone on.

Larry nodded to them.

“Alright?”

“Yeah,” Ben chuckled, “I thought we would’ve started filming by now…”

“Apparently we’re just waiting for one of the cameras. Decided to pack it in.” Larry explained. The room fell silent for a moment, until Mat noticed Larry’s brow furrow.

“Weren’t you guys there when they told us?”

Smirking, but managing not to look at one another, the two boys were amazed they were not missed.

“I mustn’t have been listening…”


End file.
